US10519181B2 - Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors - Google Patents

Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors Download PDF

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Publication number
US10519181B2
US10519181B2 US15/531,951 US201515531951A US10519181B2 US 10519181 B2 US10519181 B2 US 10519181B2 US 201515531951 A US201515531951 A US 201515531951A US 10519181 B2 US10519181 B2 US 10519181B2
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compound
chosen
groups
compound according
cells
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US20170305951A1 (en
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John L. Magnani
Arun K. Sarkar
John M. Peterson
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Glycomimetics Inc
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Glycomimetics Inc
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Assigned to GLYCOMIMETICS, INC. reassignment GLYCOMIMETICS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PETERSON, JOHN M., MAGNANI, JOHN L., SARKAR, ARUN K.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/207—Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages

Definitions

  • R 2 is chosen from —OH, —NH 2 , —OC( ⁇ O)Y 1 , —NHC( ⁇ O)Y 1 , and —NHC( ⁇ O)NHY 1 groups, wherein Y 1 is chosen from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-8 haloalkyl, C 2-8 haloalkenyl, C 2-8 haloalkynyl, C 6-18 aryl, and C 1-13 heteroaryl groups;
  • n is chosen from integers ranging from 1 to 4.
  • At least one compound of Formula (I) and/or a pharmaceutical composition comprising at least one compound of Formula (I) may be used in methods described herein for treatment and/or prevention of tumor metastasis.
  • the tumor metastasis arises from pancreatic cancer.
  • the tumor metastasis arises from prostate cancer.
  • the tumor metastasis arises from pancreatic cancer.
  • the tumor metastasis arises from breast cancer.
  • at least one additional chemotherapy agent such as gemcitabine is administered to the individual.
  • a method for releasing cells into circulating blood and enhancing retention of the cells in the blood comprising administering to a subject in need thereof an effective amount of at least one compound of Formula (I) and/or a pharmaceutical composition comprising at least one compound of Formula (I) and optionally at least one additional pharmaceutically acceptable ingredient is disclosed.
  • the method further includes collecting the released cells.
  • collecting the released cells utilizes apheresis.
  • the released cells are stem cells (e.g., bone marrow progenitor cells).
  • G-CSF is administered to the individual.
  • FIG. 7 depicts the results of a lymphatic and vacular endothelial migration toward tumor-associated fibroblasts assay by heterobifunctional Compound 9.
  • Heterobifunctional compounds for inhibition of E-selectin and the CXCR4 chemokine receptor comprising E-selectin inhibitor-Linker-CXCR4 chemokine receptor inhibitor are known in the art. Examples are disclosed, for example, in U.S. Pat. No. 8,410,066.
  • R 2 is chosen from —OH, —NH 2 , —OC( ⁇ O)Y 1 , —NHC( ⁇ O)Y 1 , and —NHC( ⁇ O)NHY 1 groups, wherein Y 1 is chosen from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-8 haloalkyl, C 2-8 haloalkenyl, C 2-8 haloalkynyl, C 6-18 aryl, and C 1-13 heteroaryl groups;
  • R 3 is chosen from —CN, —CH 2 CN, and —C( ⁇ O)Y 2 groups, wherein Y 2 is chosen from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —OZ 1 , —NHOH, —NHOCH 3 , —NHCN, and —Z 1 Z 2 groups, wherein Z 1 and Z 2 , which may be identical or different, are independently chosen from H, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-8 haloalkyl, C 2-8 haloalkenyl, and C 2-8 haloalkynyl groups, wherein Z 1 and Z 2 may join together to form a ring;
  • Linker is chosen from linker groups.
  • the compound is chosen from compounds of the following Formulae:
  • alkyl includes saturated straight, branched, and cyclic (also identified as cycloalkyl), primary, secondary, and tertiary hydrocarbon groups.
  • alkyl groups include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, secbutyl, isobutyl, tertbutyl, cyclobutyl, 1-methylbutyl, 1,1-dimethylpropyl, pentyl, cyclopentyl, isopentyl, neopentyl, cyclopentyl, hexyl, isohexyl, and cyclohexyl. Unless stated otherwise specifically in the specification, an alkyl group may be optionally substituted.
  • alkynyl includes straight and branched hydrocarbon groups comprising at least one triple bonds.
  • the triple bond of an alkynyl group can be unconjugated or conjugated with another unsaturated group.
  • alkynyl groups include ethynyl, propynyl, butyryl, pentynyl, and hexynyl. Unless stated otherwise specifically in the specification, an alkynyl group may be optionally substituted.
  • aryl includes hydrocarbon ring system group comprising 6 to 18 carbon ring atoms and at least one aromatic ring.
  • the aryl group may be a monocyclic, bicyclic, tricyclic or tetracyclic ring system, which may include fused or bridged ring systems.
  • Protecting groups may be added or removed in accordance with standard techniques, which are known to one of ordinary skill in the art and as described herein.
  • the use of protecting groups is, for example, described in detail in Green, T. W. and P. G. M. Wutz, Protective Groups in Organic Synthesis (1999), 3rd Ed., Wiley.
  • the protecting group may also be a polymer resin such as a Wang resin, Rink resin or a 2-chlorotrityl-chloride resin.
  • Non-limiting examples of such ingredients include buffers (e.g., neutral buffered saline or phosphate buffered saline), carbohydrates (e.g., glucose, mannose, sucrose or dextrans), mannitol, proteins, polypeptides, amino acids (e.g., glycine), antioxidants, chelating agents (e.g., EDTA and glutathione), stabilizers, dyes, flavoring agents, suspending agents, and preservatives.
  • buffers e.g., neutral buffered saline or phosphate buffered saline
  • carbohydrates e.g., glucose, mannose, sucrose or dextrans
  • mannitol proteins
  • proteins e.g., polypeptides
  • amino acids e.g., glycine
  • antioxidants e.g., EDTA and glutathione
  • stabilizers e.g., dyes, flavoring agents, suspending agents, and preservatives.
  • E-selectin/Ig chimera was immobilized in 96 well microtiter plates by incubation at 37° C. for 2 hours. To reduce nonspecific binding, bovine serum albumin was added to each well and incubated at room temperature for 2 hours. The plate was washed and serial dilutions of the test compounds were added to the wells in the presence of conjugates of biotinylated, sLe a polyacrylamide with streptavidin/horseradish peroxidase and incubated for 2 hours at room temperature.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
US15/531,951 2014-12-03 2015-12-01 Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors Expired - Fee Related US10519181B2 (en)

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US201462087085P 2014-12-03 2014-12-03
US15/531,951 US10519181B2 (en) 2014-12-03 2015-12-01 Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors
PCT/US2015/063191 WO2016089872A1 (en) 2014-12-03 2015-12-01 Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors

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EP (2) EP3569609A1 (zh)
JP (2) JP6689854B2 (zh)
KR (1) KR102542750B1 (zh)
CN (1) CN107108679B (zh)
AU (1) AU2015355136B2 (zh)
CA (1) CA2968391C (zh)
CY (1) CY1122038T1 (zh)
DK (1) DK3227310T3 (zh)
ES (1) ES2754549T3 (zh)
HU (1) HUE045542T2 (zh)
LT (1) LT3227310T (zh)
PL (1) PL3227310T3 (zh)
PT (1) PT3227310T (zh)
SI (1) SI3227310T1 (zh)
WO (1) WO2016089872A1 (zh)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021195465A1 (en) 2020-03-27 2021-09-30 Magnani John L Treatment of acute respiratory distress syndrome and related conditions with antagonists of e-selectin
WO2021247396A1 (en) 2020-05-31 2021-12-09 Magnani John L Compounds and methods for reduction of cancer cell burden and protection of normal hematopoiesis
WO2021257398A1 (en) 2020-06-14 2021-12-23 Magnani John L Compositions and methods for overcoming microenvironment-mediated resistance via e-selectin targeting
WO2023014690A1 (en) 2021-08-03 2023-02-09 Glycomimetics, Inc. Compositions and methods for overcoming microenvironment-mediated resistance via e-selectin targeting

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2968391C (en) 2014-12-03 2022-04-26 Glycomimetics, Inc. Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors
EP3389652B1 (en) 2015-12-14 2022-09-28 X4 Pharmaceuticals, Inc. Methods for treating cancer
WO2017151708A1 (en) 2016-03-02 2017-09-08 Glycomimetics, Inc. Methods for the treatment and/or prevention of cardiovescular disease by inhibition of e-selectin
US11337969B2 (en) 2016-04-08 2022-05-24 X4 Pharmaceuticals, Inc. Methods for treating cancer
EP3497131B1 (en) * 2016-08-08 2022-03-09 GlycoMimetics, Inc. Combination of t-cell checkpoint inhibitors with inhibitors of e-selectin or cxcr4, or with heterobifunctional inhibitors of both e-selectin and cxcr4.
CN117298287A (zh) 2016-10-07 2023-12-29 糖模拟物有限公司 高效的多聚体e-选择蛋白拮抗剂
JP7272956B2 (ja) 2017-03-15 2023-05-12 グリコミメティクス， インコーポレイテッド Ｅ－セレクチンアンタゴニストとしてのガラクトピラノシル－シクロヘキシル誘導体
WO2019108750A1 (en) 2017-11-30 2019-06-06 Glycomimetics, Inc. Methods of mobilizing marrow infiltrating lymphocytes and uses thereof
EP3732186A1 (en) 2017-12-29 2020-11-04 GlycoMimetics, Inc. Heterobifunctional inhibitors of e-selectin and galectin-3
CA3091454A1 (en) 2018-03-05 2019-09-12 Glycomimetics, Inc. Methods for treating acute myeloid leukemia and related conditions
WO2020123435A2 (en) 2018-12-10 2020-06-18 Glycomimetics, Inc. Methods of treating hiv and aids and the elimination of latent reservoirs of hiv infection using selectin, galectin, and siglec antagonists
WO2020139962A1 (en) 2018-12-27 2020-07-02 Glycomimetics, Inc. Heterobifunctional inhibitors of e-selectin and galectin-3
EP3911307A1 (en) 2019-01-14 2021-11-24 GlycoMimetics, Inc. Selectin or galectin antagonists for treating cytokine release syndrome and crs-induced neurotoxicity
BR112021021244A2 (pt) 2019-04-24 2021-12-21 Glycomimetics Inc Inibidores glicomiméticos multiméricos ligados à galactose de receptores de e-selectinas, galectina-3 e/ou quimiocina cxcr4
US20220265691A1 (en) 2019-07-12 2022-08-25 Glycomimetics, Inc. Methods for use of gene expression as an indicator of e-selectin inhibitor efficacy and clinical outcome for multiple tumor types
CA3146048A1 (en) * 2019-07-31 2021-02-04 Glycomimetics, Inc. Use of e-selectin antagonists to enhance the survival of reconstituted, bone marrow-depleted hosts

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WO2016089872A1 (en) 2016-06-09
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LT3227310T (lt) 2019-09-10
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EP3227310A4 (en) 2018-07-25
PT3227310T (pt) 2019-11-06

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